The transition from high school to college is an important phase for adolescents in social as well as academic aspects. This study examined the changes that occur in high school best friendships during the first year of college. Results revealed that during the first year in college high school best friendships declined in satisfaction, commitment, rewards, and investments. During this period there was also an increase in costs and alternatives to best friend relationships. Proximity did not influence the friendships; however, level of communication did moderate friendship deterioration. Furthermore, individuals who continued their best friendship reported engaging in more maintenance behaviors of positivity, supportiveness, self-disclosure, and interaction than individuals who reported a change in the relationship to close or casual friendship. Maintaining the best friendship also appeared to buffer adolescents from social loneliness. The results are discussed in terms of the implications of transitions on adolescent friendships.